Category: Triazoles

Research speed reading in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 41253-21-8

To 1.5 kg of crude alpha,alpha,alpha’,alpha’-tetramethyl-5-bromomethyl-1,3-benzene-diacetonitrile 5 (purity > 80%, about 3 mol) in 7.5 1 DMF 0.275 kg 1,2,4-triazole sodium (3 mol) were added. The mixture was stirred at room temperature for 1 hr. After completion, 10 1 ethyl acetate and 25 1 water were added. The mixture was stirred for about 10 minutes and then phase separated. To the aqueous layer 5 1 ethyl acetate were added. The mixture was stirred for about 10 minutes and then phase separated. The aqueous layer was discarded, and the organic layers were combined. The combined organic layers were washed with 10 1 water twice. The organic layer was concentrated to dryness to obtain the crude anastrozole 6 (90 %, purity > 60%). The crude product was purified by flash column chromatography (silica) using ethyl acetate as eluent (purity > 98%). Finally, the pre-purified anastrozole was re-crystallised from ethyl acetate/cyclohexane (1:2) to obtain 6 with a purity of more than 99.9%. Yield 34 %.

Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law. In my other articles, you can also check out more blogs about 41253-21-8, and we look forward to future research findings.

Reference:
Patent; Helm AG; EP1705168; (2006); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 135242-93-2, New Advances in Chemical Research in 2021.Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media, 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, molecular formula is C4H7N3O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

3-(2-Fluorophenyl)-6-phenyl-4H-1,2,3-triazolo[1,5-alpha]pyrimidin-5-one (77 mg, 0.25 mmol), triphenylphosphine (165 mg, 0.63 mmol) and (1-methyl-1H-1,2,4-triazol-3-yl)methanol (80 mg, 0.63 mmol) were suspended in dry tetrahydrofuran (1.5 ml).. diethyl azodicarboxylate (100 mul, 0.63 mmol) was added and a solution resulted immediately.. The reaction was stirred at room temperature for 48 hours before purification by preparative tlc (40% EtOAc/hexanes) to give a white solid which was recrystallized from ethyl acetate/hexanes to afford 3-(2-fluorophenyl)-5-(1-methyl-1H-1,2,4-triazol-3-ylmethoxy)-6-phenyl-1,2,3-triazolo[1,5-alpha]pyrimidine (49 mg, 49%) as white needles, m.p. 170-171 C.; deltaH (400 MHz, d6-DMSO) 3.84 (3H, s, NCH3), 5.57 (2H, s, OCH2), 7.35-7.41 (2H, m, ArH), 7.43-7.51 (4H, m, ArH), 7.73 (2H, dd, J=8.1 and 1.8 Hz, ArH), 8.14 (1H, td, J=7.5 and 1.8 Hz, ArH), 8.45 (1H, s, triazole CH), 9.51 (1H, s, pyrimidine CH); m/z (ES+) 402 (M+H+).

Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol.

Reference:
Patent; Merck Sharp & Dohme Ltd.; US6337331; (2002); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 16681-65-5

Compound 6. To a solution of compound 4 (5 g, 60 mmol, 1 eq.) in THF (120 mL) was added LDA (2M in THF, 45 mL, 1.5 eq.) dropwise at -78 C under N2. After the mixture was stirred at -78 C for 1 h, compound 5 (6.33 g, 90.3 mmol, 6.7 mL, 1.5eq.) was added dropwise at -78 C. The mixture was stirred at -78 C for additional 2 h under N2. The reaction mixture was then poured into ice sat. NH4Cl (100 mL) and extracted with DCM (150 mL x 5). The combined organics were washed with brine (200 mL), dried over Na2SO4, filtered, concentrated, and purified by column chromatography (SiO2, petroleum ether/ethyl acetate (1:1 to 0:1)) to afford compound 6 as a yellow solid. 1H-NMR (CDCl3, 400 MHz) delta 7.61 (s, 1H), 4.16-4.12 (m, 1H), 4.11 (s, 3H), 2.82 (d, J = 5.1 Hz, 1H), 1.37 (tq, J = 4.9, 8.2 Hz, 1H), 0.78-0.66 (m, 2H), 0.57-0.48 (m, 1H), 0.42-0.30 (m, 1H).

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 1-Methyl-1H-1,2,3-triazole, in my other articles.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD.; SNIR-ALKALAY, Irit; VACCA, Joseph; BEN-NERIAH, Yinon; (238 pag.)WO2019/155468; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 7411-23-6, New Advances in Chemical Research in 2021. As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

In a 50 mL round bottomed flask sodium hydride (60% dispersion in mineral oil) (132 mg, 3.31 mmol) was added to a colorless solution of 3,5-dibromo- lH-l,2,4-triazole (Int-1, 500 mg, 2.2 mmol) in DMF (7 ml). The resulting suspension was stirred at room temp during 30 min and 3,3,3-trifluoropropyl 4-methylbenzenesulfonate (591 mg, 2.2 mmol) solved in DMF (3 ml) was added and the reaction was stirred at 40C over night. The reaction mixture was poured into 50 mL H20 and extracted with EtOAc (3 x 50 mL). The organic layers were washed with sat NaCl (3 x 50 mL), dried over MgS04 and concentrated in vacuo. The title compound was isolated as a light yellow liquid (288 mg, 40.5 % yield). MS (ES+) m/z: 323.8 [(M+H)+].

Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about 3,5-Dibromo-1H-1,2,4-triazole.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 956317-36-5, New Advances in Chemical Research in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C10H9N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

The amine DBT salt 16 (5,67 kg, 9.09 mol) was charged to a vessel and inerted. DCM (28 L) was added, followed by 4 N Sodium Hydroxide solution (prepared from 10 N NaOH [22,4 L] and water [36 L]), The slurry was then stirred at ambient temperature for 1 h until a solution was obtained. The layers were separated and the aqueous phase treated with sodium chloride solution (10.1 kg in 20 L water). DCM (5 L) was then added and the bi-phasic mixture stirred for 10 min before separating the layers. The combined organic layers were then concentrated under reduced pressure to a 10 L volume. The solution of the free amine was used directly in the next reaction. The triazole acid 5 (13.25 kg, 65.2 mol), DCM (88 L) and DMF (1.35 L, 17.4 mol) were charged to a vessel and the resulting suspension was cooled to 0 C. Oxalyl chloride (8.28 kg, 65,2 mol) was added portion wise keeping the internal temperature between 5 and 10 C (the anhydride formed above 10 C), then the reaction was aged for 30 min at thistemperature. HPLC analysis showed acid 5 remained; an additional charge of oxalyl chloride (160 g, 1.26 mol) was made, and the solution stirred at 5 C for 30 minutes. A solution of the amine (R)-ll (16.5 kg, 62.1 mol) and triethylamine (13.19 kg, 130.0 mol) in DCM (~8 L) was added to the acid chloride over 30 minutes, keeping the internal temperature less than 15 C, The resulting slurry was aged for 30 minutes and then quenched by the addition of water (167 L) over 10 minutes, keeping the internal temperature <15 C. The lower organic layer was removed, and then concentrated under atmospheric pressure to a volume of 100 L. Assay at this stage showed 27.3 kg 1, 98%. The solution was solvent switched to MeCN (ca. 560 L, 20 mL/g) by distillation under reduced pressure at <50 C. The MeCN solution was treated with ecosorb C-941 (2.8 kg) slurried in MeCN (10 L). The resulting slurry was aged for 30 min then filtered through a Solka Flok pad and a 0.1 um cartridge filter washing with MeCN (2 x 30 L). The MeCN filtrate was concentrated under reduced pressure at <50 C to a final volume of ca 112 L. The slurry was cooled to 25 C and water (280 L) added over 40 minutes. The resulting slurry was aged at 20 C for 1 hour, then filtered, washing the cake with 5:1 water: MeCN (60 L) followed by water (40 L). The solid was dried in the vacuum oven with nitrogen purge overnight at 50 C. The final target 1 was isolated as a white solid, 26.72 kg, 95%, 98.5% ee, 99.6 LCAP. m.p. 153.1 C.[Patent; MERCK SHARP & DOHME CORP.; MERCK SHARP & DOHME LIMITED; BAXTER, Carl, A.; CLEATOR, Edward; KRSKA, Shane, W.; SHEEN, Faye; STEWART, Gavin; STROTMAN, Neil; WALLACE, Debra, J.; WRIGHT, Timothy; WO2012/148553; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 41253-21-8, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(3) Synthesis of intermediate 5-(4-chlorobenzyl)-2-methoxymethoxymethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (Compound (VII), R1 =CH3, Ym =4-Cl, G=CH2OCH3, A=N)1H-1,2,4-Triazole sodium salt (1.196g, 13.1 mmol) was dissolved in NMP (7 ml), and heated to an internal temperature of 115 degrees C. To this, 5-(4-chlorobenzyl)-2-methoxymethoxymethyl-2-methylcyclopentanone (Compound (IX), R1 =CH3, Ym =4-Cl, G=CH2OCH3) (2.60 g, 8.76 mmol) was added, and washed thoroughly with NMP (1.8 ml). After the internal temperature became 115 degrees C again, sodium t-butoxide (505 mg, 5.26 mmol) and trimethylsulfoxonium bromide (2.2379 g, 1.476 mmol) were added in portions over about 3 hours. After completion of the addition, stirring was conducted at the same temperature for 75 minutes. The reaction solution was cooled to 35 degrees C, and then, to the reaction solution, water was added and extraction with ethyl acetate was conducted. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled away and the residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate =3:1 to 0:1) for purification to obtain the desired substance. Product: 2.36 gYield: 71 %Description: Colorless viscous oil

In the meantime we’ve collected together some recent articles in this area about 41253-21-8 to whet your appetite. Happy reading!

Reference:
Patent; KUREHA CORPORATION; ARAKI, Nobuyuki; YAMAZAKI, Toru; KUSANO, Nobuyuki; IMAI, Eiyu; KANNO, Hisashi; MORI, Masaru; MIYAKE, Taiji; WO2011/70771; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 288-36-8, New Advances in Chemical Research in 2021. As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

To a mixture of 2-bromo-4-fluorobenzoic acid (30 g, 137 mmol) , cesium carbonate (89.26 g, 274 mmol) , and CuI (5.27 g, 27.4 mmol) in DMF (200 mL) was added N, N? -dimethylcyclohexane-1, 2-diamine (3.7 mL, 23.3 mmol) and 1H-1, 2, 3-triazole (18.92 g, 274 mmol) . The resulting mixture was stirred at 110 overnight, cooled, concentrated in vacuo, and diluted with water (150 mL) . The aqueous layer was washed with EtOAc (300 mL x 3) . The aqueous layer was acidified with 2 N HCl and extracted with EtOAc (300 mL x 4) . The combined organic layers were washed with brine (150 mL x 3) , dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (petroleum ether: EtOAc100: 15: 1) to provide the title compound as a solid. LRMS m/z (M+H) 208.0 found, 208.0 required.

Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about 1H-1,2,3-Triazole.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; (59 pag.)WO2016/101118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 16681-70-2, New Advances in Chemical Research in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic,A common heterocyclic compound, 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

[0622] (2S,4S)-4-Amino-5-biphenyl-4-yl-2-cyanomethylpentanoicacid ethyl ester (70 mg, 199 f.tmol) was combinedwith DMF (1 mL), HATU (76 mg, 199 flillOI), DIPEA (104f.LL, 596 f.tmol), and 3H-[1,2,3]triazole-4-carboxylic acid (22mg, 199 flillOI) and the mixture was stirred at room temperaturefor 20 minutes. The solvent was evaporated and the crudemixture was purified by normal phase chromatography(0-100% EtOAc/hexanes) to yield Compound 1 (60 mg).

Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about 1H-[1,2,3]Triazole-4-carboxylic acid.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-36-8, New Advances in Chemical Research in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

A solution of 2-bromo-3-thiophene carboxylic acid (1.50 g, 7.24 mmol), 1H-1 ,2,3- triazole (0.600 g, 8.69 mmol), potassium carbonate (2.00 g, 14.5 mmol), and copper iodide (0.138 g, 0.724 mmol) in DMF (36.2 mL) was purged subsurface with nitrogen and heated to 75 C for 4 nights. The reaction was diluted with water, washed with ether, and acidified with cone. HC1. The acidic aqueous solution was extracted 3x with ethyl acetate and the combined organic fractions were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel gradient chromatography [0-70% (1% acetic acid in ethyl acetate) in hexanes], providing the title compound as an off-white solid. LRMS m/z (M+H) 196.2 found, 196.1 required.

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Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/95442; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 288-36-8, name is 1H-1,2,3-Triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 288-36-8

But-3-yn-1-ol (49.57 g, 707.2 mmol) and triethylamine (107.7 mL, 777 mmol, dried over KOH) were dissolved in dry dichloromethane (500 mL) under a nitrogen atmosphere and cooled to 0 C. Methanesulfonyl chloride (54.8 mL, 708 mmol), dissolved in 500 mL of dry dichloromethane was added within 90 minutes while keeping the temperature below 5 C. The mixture was stirred for 3.5 hours at room temperature, then poured onto 2.5 L of ice water. The organic phase was separated and washed with 2×500 mL of water and 1×250 mL of brine and dried over sodium sulfate. The volatiles were removed to yield 94.18 g of the methane sulfonate (631.2 mmol, 89.2%) as a yellow liquid. A suspension of NaOH (37.86 g, 946.5 mmol), sodium iodide (94.65 g, 631.5 mmol) and 1H-[1,2,3]Triazole (61.03 g, 883.6 mmol) in 2-methyl-2-butanol (750 mL) was refluxed for 1 h under an inert atmosphere. After cooling to room temperature the methane sulfonate (94.18 g, 631.2 mmol) was added within 5 minutes. The resulting suspension was then heated to reflux for 3 hours, cooled to room temperature and concentrated on a rotary evaporator at 45 C. Water (500 mL) and dichloromethane (1 L) were added and the organic phase was separated, dried over sodium sulfate and the volatiles removed at 30 C. The residue was distilled at 1.5 mbar. A forerun was collected at 20-70 C. The main fraction distilled at 123-129 C. as a colorless, turbid liquid. After filtration over Celite (a pad of diatomite) 1-But-3-ynyl-1H-[1,2,3]triazole was obtained as a colorless liquid (29.8 g, 40%). The content according to GC/FID was >98%. -H-NMR (CDCl3) delta=2.05 (t, 1H, C?CH), 2.75 (dt, 2H, CH2-C?CH), 4.5 (t, 2H, CH2-triazole), 7.65 (s, 1H, triazole), 7.70 (s, 1H, triazole).

If you are hungry for even more, make sure to check my other article about 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bossenmaier, Birgit; Friebe, Walter-Gunar; Friess, Thomas; Kling, Lothar; Rueth, Matthias; Voss, Edgar; US2005/203064; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics